Cosmetic composition and an emulsion composition

ABSTRACT

A cosmetic composition and an emulsion composition respectively comprising 0.1 to 99 weight % of an oily component and 99.9 to 1 weight % of a watery component are provided and the oily component in the compositions comprises 85 or more weight % of cis-Δ9-octadecenoic acid or derivatives thereof and contains 90 weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10 weight % or less of fatty adds other than the cis-Δ9-alkenoic acid, derivatives thereof or other oily components. The cosmetic composition showing superior feeling in use and superior storage stability than conventional products and the emulsion composition showing superior stability of emulsion than conventional products can be provided because the oily component contains cis-Δ9-octadecenoic acid or derivatives thereof in a high concentration.

TECHNICAL FIELD

The present invention relates to a cosmetic composition and an emulsion composition comprising cis-Δ9-octadecenoic acid or derivatives thereof in the oily component in a high concentration.

BACKGROUND ART

A cosmetic composition containing cis-Δ9-octadecenoic acid (oleic acid) or derivatives thereof in a high concentration has not been known heretofore.

Conventional oleic acids and derivatives thereof have a bad smell, are colored, cause skin irritation, have a poor feel in use and have poor storage stability tending to further increase the poor smell color and described above.

A method of production of a high purity oleic acid was disclosed in Japanese Patent Application Laid Open No. 1986-297 (Japanese Patent Publication No. 1990-57120). The following methods of production of derivatives of the high purity oleic acid were also disclosed: a method of production of glycerol monooleate in Japanese Patent Application Laid Open No. 1987-132841, a method of production of propylene glycol monooleate in Japanese Patent Application Laid Open No. 1987-138451, a method of production of polyalkylene glycol monooleate in Japanese Patent Application Laid Open No. 1987-138452, a method of production of sorbitan monooleate in Japanese Patent Application Laid Open No. 1987-142141, a method of production of polyalkylene glycol alkyl ether oleate in Japanese Patent Application Laid Open No. 1987-153250, a method of production of polyoxyalkylene polyalcohol oleate in Japanese Patent Application Laid Open No. 1987-153251, a method of production of polyoxyalkylene polyalcohol oleate in Japanese Patent Application Laid Open No. 1987-153252, a method of production of oleic esters in Japanese Patent Application Laid Open No. 1987-153253, a method of production of polyalkylene glycol oleate in Japanese Patent Application Laid Open No. 1987-153254, a method of production of polyoxyalkylene glycol monooleate in Japanese Patent Application Laid Open No. 1987-153255 and a method of production of polyglycerol oleate in Japanese Patent Application Laid Open No. 1987-153256. It has been suggested that these high purity oleic acids and derivatives thereof have no color, no smell, are stable, cause little skin irritation and can be utilized in the field of pharmaceuticals, cosmetics, foods, synthetic resins, lubricants, biochemicals and the like. However no description can be found on specific cosmetic compositions.

The present invention has the object to provide a cosmetic composition and an emulsion composition both comprising cis-Δ9-octadecenoic acid or derivatives thereof in a high concentration and to provide a cosmetic composition having superior feeling in use and superior storage stability than conventional products and an emulsion composition showing superior emulsion stability than conventional products.

DISCLOSURE OF THE INVENTION

The present invention provides a cosmetic composition which comprises 0.1 to 99 weight % of an oily component and 99.9 to 1 weight % of a watery component, the oily component comprising 85 or more weight % of cis-Δ9-octadecenoic acid or derivatives thereof and containing 90 weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10 weight % or less of fatty acids other than the cis-Δ9-alkenoic acid, derivatives thereof or other oily components.

The present invention also provides an emulsion composition which comprises 0.1 to 99 weight % of an oily component and 99.9 to 1 weight % of a watery component, the oily component comprising 85 or more weight % of cis-Δ9-octadecenoic acid or derivatives thereof, containing 90 weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof and 10 weight % or less of fatty acids other than the cis-Δ9-alkenoic acid, derivatives thereof or other oily components and having an oily substance insoluble in the watery component and a surfactant which is dissolved or emulsified in the watery component.

THE MOST PREFERRED EMBODIMENT TO CARRY OUT THE INVENTION

The invention is described in more detail in the following.

The ratio of the oily component and the watery component is 0.1 to 99 weight %:99.9 to 1 weight %. However, this ratio is adopted for general cosmetic compositions and the ratio is different depending on the kind of the cosmetic composition. For example, the following ratios can be adopted: for skin lotion, 0.5 to 20 weight %:99.5 to 80 weight %; for skin cream, 10 to 85 weight %:90 to 15 weight %; for milk lotion, 3 to 50 weight %:97 to 50 weight %; and for cleansing foam, 30 to 70 weight %: 70 to 30 weight %.

The cis-Δ9-alkenoic acid in the invention is a fatty acid having one cis-unsaturated bond at the 9-position, such as cis-Δ9-octadecenoic acid (generally called oleic acid), cis-Δ9-hexadecenoic acid (generally called palmitoleic acid) and the like.

The derivatives of the cis-Δ9-alkenoic acid (including cis-Δ9-octadecenoic acid) comprise the following derivatives:

(1) Salts: salts of alkali metals, such as sodium, potassium and the like; ammonium salts; morpholine salts; salts of alkylamines, such as methylamine, ethylamine, butylamine and the like; salts of alkanolamines, such as monoethanolamine, diethanolamine, triethanolamine, triisopropanolamine, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol; salts of basic amino acids, such as arginine and the like; and the like salts;

(2) Amides (these amides are cis-Δ9-alkenoic acid amides): amides with alkylamines or alkenylamines, such as methylamine, ethylamine, butylamine, cis-Δ9-alkenyl amines and the like; amides with alkanolamines, such as monoethanolamine, diethanolamine, isopropanolamine, 2-amino-2-methyl-1-propanol, 2-amino-2-methyl-1,3-propanediol and the like; polyoxyethylated compounds and polyoxypropylated compounds of these amides; amides and salts of amides of amino acids, such as glutamic acid and the like; amides with sodium N-methyltaurine; cis-Δ9-alkenoyl peptides, such as cis-Δ9-alkenoyl collagen and the like; and the like amides;

(3) Esters: esters with monohydric alcohols, such as methanol, ethanol, propanol, isopropanol, butanol, neopentanol, hexanol, octanol, 2-ethylhexanol, nonanol, isononanol, decanol, dodecanol, isotridecanol, tetradecanol, hexadecanol, isohexadecanol, hexyldecanol, octadecanol, isooctadecanol, eicosanol, 2-octyldodecanol, docosanol, octacosanol, triacontanol, aryl alcohol, hexadecenol, cis-Δ9-octadecenol, decocenol, cyclohexanol, lanolin alcohol, terpene alcohol, benzyl alcohol and the like, and esters with polyoxyethylated compounds or polyoxypropylated compounds of the monohydric alcohols; esters with polyhydric alcohols, such as ethylene glycol, propylene glycol, butylene glycol, glycerol, polyglycerols, trimethylolpropane, pentaerythritol, sorbitol, mannitol, sorbitan and the like, and esters with polyoxyethylated compounds or polyoxypropylated compounds of the polyhydric alcohols; esters with sugars, such as glucose, sucrose and the like; esters with sterols, such as cholesterol, cholestanol, sitosterol and the like; esters and salts with other hydroxyl compounds, such as tocopherol, oryzanol, guaiacol, gossypol, terpene alcohols, fiuoroalcohols, isethionic acid and the like; phospholipids in which the acyl group of a cis-Δ9-alkenoic acid is introduced; and the like esters;

(4) Derivatives of cis-Δ9-alkenols: cis-Δ9-alkenols derived from cis-Δ9alkenoic acids; phosphoric esters, sulfuric esters, polyoxyethylated compounds, polyoxypropylated compounds, polyoxyethylated phosphoric esters, polyoxyethylated sulfuric esters, polyoxypropylated phosphoric esters and polyoxypropylated sulfuric esters of the cis-Δ9-alkenols and salts of these compounds; esters, partial esters and partial ester salts of cis-Δ9-alkenyl alcohols with saturated, unsaturated, straight chain, branched chain, monovalent or polyvalent carboxylic acids or hydroxylated carboxylic acids derived from these carboxylic acid, such as ethanoic acid, butanoic acid, 2-ethylhexanoic acid, dodecanoic acid, octadecanoic acid, cis-Δ9-octadecenoic acid, succinic acid, adipic acid, sebacic acid, maleic acid, oxalic acid, citric acid, malic acid and the like; ethers of cis-Δ9-alkenols with alcohols, sugars or hydroxyl compounds described in (3) in the above; and the like compounds; and

(5) Derivatives of cis-Δ9-alkenylamines: salts of cis-Δ9-alkenylamines derived from cis-Δ9-alkenoic acids with acids, such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, ethanoic acid and the like; quaternary ammonium salts having a cis-Δ9-alkenyl group; quaternary ammonium betaine having a cis-Δ9-alkenyl group; and the like compounds.

As shown in the above, the derivatives of cis-Δ9-alkenoic acid of the oily component of the invention is an oily substance insoluble in the watery component or a surfactant which is dissolved or emulsified in the watery component. Therefore, the cosmetic composition of the invention includes a composition having two separated layers composed of the oily substance and the watery component, a homogeneous composition composed of the surfactant and the watery component and a homogeneous transparent or turbid composition having the oily substance dissolved, emulsified or dispersed in the watery component by the effect of the surface active agent.

Preferable examples of the derivatives of the cis-Δ9-alkenoic acids as the oily substance are esters of cis-Δ9-octadecenoic acid with ethanol, isopropanol, cis-Δ9-hexadecenol, cis-Δ9-octadecenol, isooctadecanol, cholesterol and tocopherol; glycerol tri-cis-Δ9-octadecenoate; cis-Δ9-octadecenoic acid; cis-Δ9-octadecenol and the like. Preferable examples of the derivatives of the cis-Δ9-alkenoic acids as the surfactant are monoesters of cis-Δ9-octadecenoic acid and glycerol or polyglycerol, sorbitan mono- or sesqui-cis-Δ9-octadecenoate, polyoxyethylated sorbitan mono-cis-Δ9-octadecenoate, polyoxyethylated sorbitol tri- or tetra-cis-Δ9-octadecenoate, polyoxyethylene glycol mono-cis-Δ9-octadecenoate and polyoxyethylated cis-Δ9-octadecenyl ether. The particularly preferable examples for both of the oily substance and the surfactant are esters of cis-Δ9-octadecenoic acid.

In the invention, cis-Δ9-alkenoic acid and the derivative thereof which are the oily component insoluble in the watery component can be solubilized or emulsified in the watery component much more easily by using the surfactant of the derivatives of cis-Δ9-alkenoic acid in comparison to using other surface active agents and the stability is much more excellent. The weight ratio of the oily substance and the surfactant in this case is varied depending on the kinds and the ratio of the oily component and the surfactant, other additives and the like. The ratio is generally in the range of 99 to 1:1 to 99 and preferably in the range of 97 to3:3 to 97.

The oily component other than those described above are all kinds of oily components other than the cis-Δ9-alkenoic acids and the derivatives thereof. Examples are natural and synthetic oily substances, such as fatty acids and derivatives thereof other than the cis-Δ9-alkenoic acids, paraffin, kerosene, squalane, plant oils, animal oils, lanoline, haze wax, hexadecanol, isooctadecanol, silicone oils, fiuorohydrocarbons, polyoxypropylated ethers, cholesterol, tocopherol and the like; surface active agents derived from fatty acids other than the cis-Δ9-alkenoic acids, such as dodecandiethanolamide and the like; other surface active agents like polyoxyethylated alkylphenyl ether; and the like.

The watery component functions as the moisturizing agent and the examples include water, of course, and compounds which can be mixed with water in any ratio, such as alcohols like ethanol, isopropanol, ethylene glycol, propylene glycol, 1,3-butylene glycol, polyethylene glycols, glycerol, sorbitol, polyglycerols, polyvinyl alcohols and the like; sugars like glucose, sucrose and the like; mucopolysaccharides like hyaluronic acid and the like; amino acids like glutamic acid and the like; proteins like collagen and the like; and the like compounds.

When other cis-Δ9-alkenoic acids such as palmitoleic acid are present together with cis-Δ9-octadecenoic acid, the other cis-Δ9-alkenoic acids exhibit the same effect as that of cis-Δ9-octadecenoic acid. The oily component contains 85 weight % or more of cis-Δ9-octadecenoic acid and 90 weight % or more of the cis-Δ9-alkenoic acid, preferably 90 weight % or more of cis-Δ9-octadecenoic acid and 93 weight % or more of the cis-Δ9-alkenoic acid, more preferably 95 weight % or more of cis-Δ9-octadecenoic acid and 97 weight % or more of the cis-Δ9-alkenoic acid and most preferably 97 weight % or more of cis-Δ9-octadecenoic acid and 99 weight % or more of the cis-Δ9-alkenoic acid. When the content of cisΔ9-octadecenoic acid is less than 85 weight % or the content of the cis-Δ9-alkenoic acid is less than 90 weight %, the feeling in use of the cosmetic composition is not satisfactory.

The cosmetic composition of the invention may comprise components generally added to cosmetic compositions, such as drugs like vitamins, antibiotics and the like, nutrients, ultraviolet ray absorbents, carbon black, titanium oxide, iron oxide, metallic soaps, calcium carbonate, silica, talc, colors, perfumes and the like, in addition to the oily component and the watery component described above.

The cosmetic composition of the invention takes the form of liquid, cream, gel or solid depending on the mixed composition. It is used as skin lotion, cosmetic oil, milk lotion, lipstick, hair liquid, hair cream, hair growth agent, foundation, various kinds of cream and the like.

The emulsion composition of the invention may comprise various kinds of additives generally added to emulsion compositions.

The method of preparation of the cosmetic composition and the emulsion composition of the invention can be performed by compounding the components described above. The order of the addition of the components is not particularly limited and components can be suitably selected and added. The compounded components are suitably mixed by using various kinds of mixer, various kinds of dispersing machine, various kinds of emulsifying machine or the like to prepare the cosmetic composition and the emulsion composition of the invention.

The reason that the stability of the product in the invention is very excellent when the derivative of cis-Δ9-octadecenoic acid is used as the surfactant to emulsify or solubilize in the watery component cis-Δ9-octadecenoic acid or the derivative which is insoluble in the watery component can be considered as following: when the concentration of cis9-octadecenoic acid or the derivative is high, mutual orientation and cohesion of the cis-Δ9-octadecenoyl group or the cis-Δ9-octadecenyl group in the molecule is considered to be enhanced and the molecular structure proper to the molecule is efficiently exhibited; this is considered to have the effect on the better feeling in use of the cosmetic composition comprising cis-Δ9-octadecenoic acid or the derivative in a high concentration.

The cosmetic composition of the invention comprising cis-Δ9-octadecenoic acid or the derivatives thereof in the oily component in a high concentration provides very excellent feeling in use and the result is remarkably superior than the cosmetic compositions comprising cis-9-octadecenoic acid or the derivatives thereof in a low concentration.

Cosmetic compositions prepared by using commercial oleic acid or derivatives thereof having low concentrations of cis-Δ9-octadecenoic acid as the material are colored or generate smell with passage of time. The cosmetic composition of the invention does not have such drawback.

The emulsion composition of the invention comprising cis-Δ9-octadecenoic acid or the derivative thereof in the oily component in a high concentration has a very excellent stability of the emulsion.

EXAMPLE

The invention is described with reference to examples. However, the invention is by no means limited by the examples.

In Examples and Comparative Examples, oleic acid or oleic acid derivatives containing various kinds of cis-Δ9-octadecenoic acid and derivatives thereof were used as the oily component. The concentration was represented by the purity of cis-Δ9-octadecenoic acid or a cis-Δ9-alkenoic acid in the oleic acid.

When the concentration of cis-Δ9-octadecenoic acid or its derivative is varied in a cornposition using two or more kinds of oleic acid or oleic acid derivatives, the oleic acids or the oleic acid derivatives having the same purity of the cis-Δ9-octadecenoic acid were used for compounding in the composition.

In the Examples and Comparative Examples, "%" means "weight %". The oleic acid or the oleic acid derivative containing 57% of cis-Δ9-octadecenoic acid and 66 weight % of cis-Δ9-alkenoic acid used in Comparative Examples is a commercial oleic acid or a derivative from the commercial oleic acid.

Method of evaluation of the cosmetic composition, method of evaluation of storage stability of an emulsion composition and method of analysis of purity of a cis-Δ9-alkenoic acid containing cis-Δ9-octadecenoic acid are described in the following.

Method of evaluation of the feeling in use

Overall feeling in use including all of smell, extension, refreshing feeling and emollient effect was evaluated by 20 women panellers and the result is shown by the number of the panellers whose answer was good.

Method of evaluation of storage stability of an emulsion composition

An oily component (including oily substances and surfactants) and a watery component were mixed by shaking mildly and then emulsified by using a homogenizer (DX-3 type, a product of Nippon Seiki Seisakusho Co., Ltd.) at 10,000 rpm for 15 minutes. Condition of the emulsion was evaluated by visual observation according to the following criterion:

    ______________________________________                                         stable:       emulsified in a stable condition                                 slightly separated:                                                                          slightly separated                                               separated:    completely separated into two phases                             ______________________________________                                    

Method of analysis of purity

Analysis was conducted by using an apparatus for gas chromatography (GC-9A, a product of Shimazu Seisakusho Co., Ltd.) equipped with capillary columns which can separate isomers having different positions of a double bond and different steric structures (SP-2560:0.25 mm×100 m, a product of Supelco Inc.).

Examples 1 to 5 and Comparative Examples 1 to 3

Skin lotions were prepared by using N-oleoyl-L-glutamic acids which are oleic acid derivatives having different purities shown in Table 1 as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 1.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily component                                                                 surfactant: N-oleoyl-L-glutamic acid                                                                   3%                                                     watery components                                                              ethanol                10%                                                     purified water         85%                                                     sorbitol                2%                                                     ______________________________________                                    

                  TABLE 1                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 1                                                                               99.9         100         19                                           Example 2                                                                               99           99.5        17                                           Example 3                                                                               95           97          15                                           Example 4                                                                               90           93          15                                           Example 5                                                                               85           90          13                                           Comparative                                                                             80           86           7                                           Example 1                                                                      Comparative                                                                             70           78           1                                           Example 2                                                                      Comparative                                                                             57           66           0                                           Example 3                                                                      ______________________________________                                    

Examples 6 to 10 and Comparative Examples 4 to 6

Cleansing creams were prepared by using monosodium N-oleoylglutamates which are oleic acid derivatives having different purities shown in Table 2 as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 2.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily component                                                                 surfactant: monosodium N-oleoylglutamate                                                                45%                                                   watery components                                                              purified water           50%                                                   polyethylene glycol       5%                                                   ______________________________________                                    

                  TABLE 2                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 6                                                                               99.9         100         20                                           Example 7                                                                               99           99.5        18                                           Example 8                                                                               95           97          16                                           Example 9                                                                               90           93          15                                           Example 10                                                                              85           90          13                                           Comparative                                                                             80           86          10                                           Example 4                                                                      Comparative                                                                             70           78           7                                           Example 5                                                                      Comparative                                                                             57           66           0                                           Example 6                                                                      ______________________________________                                    

Examples 11 to 15 and Comparative Examples 7 to 9

Skin lotions were prepared by using glycerol monooleates which are oleic acid derivatives having different purities shown in Table 3 and polyoxyethylated (25 mols) oleyl ethers which are oleic acid derivatives having the same purities as those of the corresponding glycerol monooleates as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 3.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily component                                                                 surfactants: glycerol monooleate                                                                       3%                                                     polyoxyethylated (25 mols) oleyl ether                                                                 2%                                                     watery components                                                              ethanol                 10%                                                    purified water          82%                                                    sorbitol                3%                                                     ______________________________________                                    

                  TABLE 3                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 11                                                                              99.9         100         20                                           Example 12                                                                              99           99.5        19                                           Example 13                                                                              95           97          18                                           Example 14                                                                              90           93          18                                           Example 15                                                                              85           90          15                                           Comparative                                                                             80           86           9                                           Example 7                                                                      Comparative                                                                             70           78           0                                           Example 8                                                                      Comparative                                                                             57           66           0                                           Example 9                                                                      ______________________________________                                    

Examples 16 to 20 and Comparative Examples 10 to 12

Skin lotions were prepared by using L-α-dioleoyl phosphatidyl cholines which are oleic acid derivatives having different purities shown in Table 4 and polyoxyethylated (20 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding L-α-dioleoyl phosphatidyl cholines as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 4.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily component                                                                 surfactants: L-α-dioleoyl phosphatidyl choline                                                     2%                                                   polyoxyethylated (20 mols) sorbitan                                                                      1%                                                   monooleate                                                                     watery components                                                              ethanol                   15%                                                  purified water            80%                                                  propylene glycol          2%                                                   ______________________________________                                    

                  TABLE 4                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadenoic acid                                                                           alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 16                                                                              99.9         100         20                                           Example 17                                                                              99           99.5        20                                           Example 18                                                                              95           97          18                                           Example 19                                                                              90           93          15                                           Example 20                                                                              85           90          13                                           Comparative                                                                             80           86           8                                           Example 10                                                                     Comparative                                                                             70           78           0                                           Example 11                                                                     Comparative                                                                             57           66           0                                           Example 12                                                                     ______________________________________                                    

Examples 21 to 25 and Comparative Examples 13 to 15

Skin lotions were prepared by using N-oleoyl-L-glutamic acids which are oleic acid derivatives having different purities shown in Table 5 and hexaglycerol monooleates which are oleic acid derivatives having the same purities as those of the corresponding N-oleoyl-L-glutamic acids as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 5.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily component                                                                 surfactants: N-oleoyl-L-glutamic acid                                                                  2%                                                     hexaglycerol monooleate                                                                                3%                                                     watery components                                                              ethanol                10%                                                     purified water         85%                                                     ______________________________________                                    

                  TABLE 5                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 21                                                                              99.9         100         20                                           Example 22                                                                              99           99.5        19                                           Example 23                                                                              95           97          16                                           Example 24                                                                              90           93          14                                           Example 25                                                                              85           90          11                                           Comparative                                                                             80           86           3                                           Example 13                                                                     Comparative                                                                             70           78           0                                           Example 14                                                                     Comparative                                                                             57           66           0                                           Example 15                                                                     ______________________________________                                    

Examples 26 to 30 and Comparative Examples 16 to 18

Shaking lotions separated to two phases were prepared by using isooctadecanyl oleates which are oleic acid derivatives having different purities shown in Table 6 as the oily substance and polyoxyethylated (20 mols) sorbitan tetraoleates which are oleic acid derivatives having the same purities as those of the corresponding isooctadecanyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 6.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: isooctadecanyl oleate                                                                     8      %                                            surfactant: polyoxyethylated (20 mols) sorbitan                                                           0.2    %                                            tetraoleate                                                                    watery components                                                              purified water             79.8   %                                            ethanol                    10     %                                            sorbitol                   1      %                                            glycerol                   1      %                                            ______________________________________                                    

                  TABLE 6                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 26                                                                              99.9         100         20                                           Example 27                                                                              99           99.5        20                                           Example 28                                                                              95           97          18                                           Example 29                                                                              90           93          17                                           Example 30                                                                              85           90          13                                           Comparative                                                                             80           86           4                                           Example 16                                                                     Comparative                                                                             70           78           0                                           Example 17                                                                     Comparative                                                                             57           66           0                                           Example 18                                                                     ______________________________________                                    

Examples 31 to 35 and Comparative Examples 19 to 21

Skin creams were prepared by using hexadecenyl oleates which are oleic acid derivatives having different purities shown in Table 7 as the oily substance and polyoxyethylated (10 mols) oleyl ethers which are oleic acid derivatives having the same purities as those of the corresponding hexadecenyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 7.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: hexadecenyl oleate                                                                         70%                                                surfactant: polyoxyethylated (10 mols) oleyl ether                                                          5%                                                watery components                                                              purified water              22%                                                glycerol                     3%                                                ______________________________________                                    

                  TABLE 7                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 31                                                                              99.9         100         20                                           Example 32                                                                              99           99.5        20                                           Example 33                                                                              95           97          19                                           Example 34                                                                              90           93          18                                           Example 35                                                                              85           90          13                                           Comparative                                                                             80           86           7                                           Example 19                                                                     Comparative                                                                             70           78           0                                           Example 20                                                                     Comparative                                                                             57           66           0                                           Example 21                                                                     ______________________________________                                    

Examples 36 to 40 and Comparative Examples 12 to 24

Skin creams were prepared by using ethyl oleates which are oleic acid derivatives having different purities shown in Table 8 as the oily substance and diglycerol monooleates which are oleic acid derivatives having the same purities as those of the corresponding ethyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 8.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: ethyl oleate                                                                         65%                                                      surfactant: diglycerol monooleate                                                                     5%                                                      watery component                                                               purified water        30%                                                      ______________________________________                                    

                  TABLE 8                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 36                                                                              99.9         100         20                                           Example 37                                                                              99           99.5        20                                           Example 38                                                                              95           97          18                                           Example 39                                                                              90           93          18                                           Example 40                                                                              85           90          14                                           Comparative                                                                             80           86           7                                           Example 22                                                                     Comparative                                                                             70           78           1                                           Example 23                                                                     Comparative                                                                             57           66           0                                           Example 24                                                                     ______________________________________                                    

Examples 41 to 45 and Comparative Examples 25 to 27

Oleyl oleates of different purities were prepared by esterification of oleic acids having different purities shown in Table 9 with oleyl alcohols having the same purities as those of the corresponding oleic acids which were prepared by reduction of the oleic acids. Skin creams were prepared by using the oleyl oleates as the oily substance and glycerol monooleates and sucrose monooleates which are oleic acid derivatives having the same purities as those of the corresponding oleyl oleates, respectively, as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 9.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: oleyl oleate                                                                             40%                                                  surfactants: glycerol monooleate                                                                          2.5%                                                sucrose monooleate         1.5                                                 watery components                                                              purified water            53%                                                  propylene glycol           3%                                                  ______________________________________                                    

                  TABLE 9                                                          ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 41                                                                              99.9         100         20                                           Example 42                                                                              99           99.5        19                                           Example 43                                                                              95           97          18                                           Example 44                                                                              90           93          16                                           Example 45                                                                              85           90          13                                           Comparative                                                                             80           86           8                                           Example 25                                                                     Comparative                                                                             70           78           0                                           Example 26                                                                     Comparative                                                                             57           66           0                                           Example 27                                                                     ______________________________________                                    

Examples 46 to 50 and Comparative Examples 28 to 30

Skin creams were prepared by using glycerol trioleates which are oleic acid derivatives having different purities shown in Table 10 as the oily substance and sorbitan sesquioleates and polyoxyethylated (20 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding glycerol trioleates, respectively, as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 10.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: glycerol trioleate                                                                       75%                                                  surfactants: sorbitan sesquioleate                                                                        3.5%                                                polyoxyethylated (20 mols) sorbitan                                                                       1.5%                                                monooleate                                                                     watery components                                                              purified water            17%                                                  sorbitol                   3%                                                  ______________________________________                                    

                  TABLE 10                                                         ______________________________________                                                                       evaluation of                                           purity of cis-Δ9-                                                                   purity of cis-Δ9-                                                                    feeling in use                                          octadecenoic acid                                                                         alkenoic acid                                                                              (number of                                              (%)        (%)         persons)                                         ______________________________________                                         Example 46                                                                              99.9         100         19                                           Example 47                                                                              99           99.5        19                                           Example 48                                                                              95           97          18                                           Example 49                                                                              90           93          15                                           Example 50                                                                              85           90          13                                           Comparative                                                                             80           86           7                                           Example 28                                                                     Comparative                                                                             70           78           0                                           Example 29                                                                     Comparative                                                                             57           66           0                                           Example 30                                                                     ______________________________________                                    

Examples 51 to 55 and Comparative Examples 31 to 33

Skin creams were prepared by using 2-octyldodecyl oleates which are oleic acid derivatives having different purities shown in Table 11 as the oily substance and pentaerythritol monooleates and polyoxyethylated (20 mols) oleyl ethers which are oleic acid derivatives having the same purities as those of the corresponding 2-octyldodecyl oleates, respectively, as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 11.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: 2-octyldodecyl oleate                                                                  20%                                                    surfactants: pentaerythritol monooleate                                                                2%                                                     polyoxyethylated (20 mols) oleyl                                                                       1%                                                     ether                                                                          watery components                                                              purified water          72%                                                    glycerol                5%                                                     ______________________________________                                    

                  TABLE 11                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 51     99.9       100      20                                          Example 52     99         99.5     19                                          Example 53     95         97       18                                          Example 54     90         93       18                                          Example 55     85         90       14                                          Comparative Example 31                                                                        80         86       9                                           Comparative Example 32                                                                        70         78       7                                           Comparative Example 33                                                                        57         66       0                                           ______________________________________                                    

Examples 56 to 60 and Comparative Examples 34 to 36

Milk lotions were prepared by using oleic acids having different purities shown in Table 12 and cholesterol oleates which are derivatives of these oleic acids as the oily substances and L-α-dioleoyl phosphatidyl cholines which are oleic acid derivatives having the same purities as those of the corresponding oleic acids as the surfactant according to the formulation described below and the feeling in use was evaluated, The results are shown in Table 12.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substances: oleic acid                                                                              2%                                                   cholesterol oleate        10                                                   surfactant: L-α-dioleoyl phosphatidyl choline                                                      2%                                                   watery component                                                               purified water            86%                                                  ______________________________________                                    

                  TABLE 12                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 56     99.9       100      20                                          Example 57     99         99.5     19                                          Example 58     95         97       18                                          Example 59     90         93       18                                          Example 60     85         90       15                                          Comparative Example 34                                                                        80         86       10                                          Comparative Example 35                                                                        70         78       7                                           Comparative Example 36                                                                        57         66       0                                           ______________________________________                                    

Examples 61 to 65 and Comparative Examples 37 to 39

Milk lotions were prepared by using glycerol dioleates which are oleic acid derivatives having different purities shown in Table 13 as the oily substance and L-arginine oleates which are oleic acid derivatives having the same purities as those of the corresponding glycerol dioleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 13.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: glycerol dioleate                                                                    15%                                                      surfactant: L-arginine oleate                                                                        1%                                                       watery component                                                               purified water        84%                                                      ______________________________________                                    

                  TABLE 13                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 61     99.9       100      20                                          Example 62     99         99.5     20                                          Example 63     95         97       18                                          Example 64     90         93       18                                          Example 65     85         90       18                                          Comparative Example 37                                                                        80         86       14                                          Comparative Example 38                                                                        70         78       9                                           Comparative Example 39                                                                        57         66       0                                           ______________________________________                                    

Examples 66 to 70 and Comparative Examples 40 to 42

Milk lotions were prepared by using tocopherol oleates which are oleic acid derivatives having different purities shown in Table 14 as the oily substance and sucrose monooleates which are oleic acid derivatives having the same purities as those of the corresponding tocopherol oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 14.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: tocopherol oleate                                                                    10%                                                      surfactant: sucrose monooleate                                                                       3%                                                       watery components                                                              purified water        84%                                                      glycerol              3%                                                       ______________________________________                                    

                  TABLE 14                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 66     99.9       100      20                                          Example 67     99         99.5     19                                          Example 68     95         97       18                                          Example 69     90         93       15                                          Example 70     85         90       13                                          Comparative Example 40                                                                        80         86       7                                           Comparative Example 41                                                                        70         78       0                                           Comparative Example 42                                                                        57         66       0                                           ______________________________________                                    

Examples 71 to 75 and Comparative Examples 43 to 45

Cleansing creams were prepared by using isopropyl oleates which are oleic acid derivatives having different purities shown in Table 15 as the oily substance and polyoxyethylated (20 mols) oleyl ethers and polyoxyethylated (5 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding isopropyl oleates, respectively, as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 15.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: isopropyl oleate                                                                           80%                                                surfactants: polyoxyethylated (20 mols) oleyl ether                                                        3%                                                 polyoxyethylated (5 mols) sorbitan                                                                         2%                                                 monooleate                                                                     watery component                                                               purified water              15%                                                ______________________________________                                    

                  TABLE 15                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 71     99.9       100      20                                          Example 72     99         99.5     20                                          Example 73     95         97       18                                          Example 74     90         93       18                                          Example 75     85         90       13                                          Comparative Example 43                                                                        80         86       7                                           Comparative Example 44                                                                        70         78       0                                           Comparative Example 45                                                                        57         66       0                                           ______________________________________                                    

Examples 76 to 80 and Comparative Examples 46 to 48

Cleansing foams were prepared by using oleyl alcohols which are oleic acid derivatives having different purities shown in Table 16 as the oily substance and potassium oleates which are oleic acid derivatives having the same purities as those of the corresponding oleyl alcohols as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 16.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: oleyl alcohol                                                                       3%                                                        surfactant: potassium oleate                                                                        40%                                                       watery component                                                               purified water       57%                                                       ______________________________________                                    

                  TABLE 16                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 76     99.9       100      20                                          Example 77     99         99.5     19                                          Example 78     95         97       18                                          Example 79     90         93       18                                          Example 80     85         90       14                                          Comparative Example 46                                                                        80         86       9                                           Comparative Example 47                                                                        70         78       0                                           Comparative Example 48                                                                        57         66       0                                           ______________________________________                                    

Examples 81 to 85 and Comparative Examples 49 to 51

Cleansing foams were prepared by using ethylene glycol monooleates which are oleic acid derivatives having different purities shown in Table 17 as the oily substance and monosodium N-oleoylglutamates which are oleic acid derivatives having the same purities as those of the corresponding ethylene glycol monooleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 17.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: ethylene glycol monooleate                                                              5%                                                    surfactant: monosodium N-oleoylglutamate                                                                40%                                                   watery components                                                              purified water           50%                                                   polyethylene glycol      5%                                                    ______________________________________                                    

                  TABLE 17                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 81     99.9       100      20                                          Example 82     99         99.5     19                                          Example 83     95         97       18                                          Example 84     90         93       18                                          Example 85     85         90       14                                          Comparative Example 49                                                                        80         86       8                                           Comparative Example 50                                                                        70         78       7                                           Comparative Example 51                                                                        57         66       0                                           ______________________________________                                    

Examples 86 to 90 and Comparative Examples 52 to 54

Foundations of milk lotion were prepared by using isooctadecanyl oleates which are oleic acid derivatives having different purities shown in Table 18 as the oily substance and triethanolamine oleates which are oleic acid derivatives having the same purities as those of the corresponding isooctadecanyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 18.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: isooctadecanyl oleate                                                                    18%                                                  surfactant: triethanolamine oleate                                                                       5%                                                   watery component                                                               purified water            64.9%                                                pigments                                                                       titanium dioxide          8%                                                   talc                      4%                                                   color                     0.1%                                                 ______________________________________                                    

                  TABLE 18                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 86     99.9       100      20                                          Example 87     99         99.5     20                                          Example 88     95         97       18                                          Example 89     90         93       18                                          Example 90     85         90       18                                          Comparative Example 52                                                                        80         86       13                                          Comparative Example 53                                                                        70         78       8                                           Comparative Example 54                                                                        57         66       0                                           ______________________________________                                    

Examples 91 to 95 and Comparative Examples 55 to 57

Lipsticks were prepared by using docosenyl oleates and octacosanyl oleates which are oleic acid derivatives having different purities shown in Table 19, respectively, as the oily substances and glycerol monooleates which are oleic acid derivatives having the same purities as those of the corresponding docosenyl oleates and octacosanyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 19.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substances: docosenyl oleate                                                                         42%                                                 octacosanyl oleate         15%                                                 surfactant: glycerol monooleate                                                                           30%                                                 watery component                                                               glycerol                   3%                                                  pigments                                                                       titanium dioxide           1%                                                  red pigment No. 201        1%                                                  red pigment No. 202        1%                                                  blue pigment No. 1 aluminum chelate                                                                       0.5%                                                mica titanium              6.5%                                                ______________________________________                                    

                  TABLE 19                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 91     99.9       100      20                                          Example 92     99         99.5     19                                          Example 93     95         97       18                                          Example 94     90         93       18                                          Example 95     85         90       14                                          Comparative Example 55                                                                        80         86       9                                           Comparative Example 56                                                                        70         78       7                                           Comparative Example 57                                                                        57         66       0                                           ______________________________________                                    

Examples 96 to 100 and Comparative Examples 58 to 60

Hair creams were prepared by using octadecyl oleates which are oleic acid derivatives having different purities shown in Table 20 as the oily substance and polyoxyethylene (10 mols) glycol monooleates which are oleic acid derivatives having the same purities as those of the corresponding octadecyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 20.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: octadecyl oleate                                                                         15%                                                  surfactant: polyoxylethylene (10 mols) glycol                                                            5%                                                   monooleate                                                                     watery components                                                              purified water            75%                                                  propylene glycol          5%                                                   ______________________________________                                    

                  TABLE 20                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 96     99.9       100      20                                          Example 97     99         99.5     19                                          Example 98     95         97       18                                          Example 99     90         93       18                                          Example 100    85         90       13                                          Comparative Example 58                                                                        80         86       8                                           Comparative Example 59                                                                        70         78       0                                           Comparative Example 60                                                                        57         66       0                                           ______________________________________                                    

Examples 101 to 105 and Comparative Examples 61 to 63

Hair growth agents were prepared by using ethyl oleates which are oleic acid derivatives having different purities shown in Table 21 as the oily substance and glycerol monooleates which are oleic acid derivatives having the same purities as those of the corresponding ethyl oleates as the surfactant according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 21.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: ethyl oleate                                                                            3%                                                    surfactant: glycerol monooleate                                                                         2%                                                    watery component                                                               ethanol                  93.4%                                                 hair growth components                                                         cepharanthin             1%                                                    hinokitiol               0.1%                                                  tocopherol nicotinate    0.5%                                                  ______________________________________                                    

                  TABLE 21                                                         ______________________________________                                                                            evaluation                                                 purity of  purity of                                                                               of feeling                                                 cis-Δ9-                                                                             cis-Δ9-                                                                           in use                                                     octadecenoic                                                                              alkenoic (number of                                                 acid (%)   acid (%) persons)                                    ______________________________________                                         Example 101    99.9       100      20                                          Example 102    99         99.5     20                                          Example 103    95         97       19                                          Example 104    90         93       18                                          Example 105    85         90       14                                          Comparative Example 61                                                                        80         86       7                                           Comparative Example 62                                                                        70         78       1                                           Comparative Example 63                                                                        57         66       0                                           ______________________________________                                    

Examples 106 to 110 and Comparative Examples 64 to 66

Hair growth agents were prepared by using palmityl oleates which are oleic acid derivatives having different purities shown in Table 22 as the oily substance and polyoxyethylene (10 mols) oleyl ether phosphoric acid sodium salts which are oleic acid derivatives having the same purities as those of the corresponding palmityl oleates as the surfactants according to the formulation described below and the feeling in use was evaluated. The results are shown in Table 22.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: palmityl oleate                                                                             2%                                                surfactants: polyoxyethylene (10 mols) oleyl ether                                                          2%                                                phosphoric acid sodium salt                                                    watery components                                                              ethanol                      70%                                               purified water               24.4%                                             hair growth components                                                         capronium chloride           1%                                                extract of Japanese green gentian                                                                           0.1%                                              α-tocopherol           0.5%                                              ______________________________________                                    

                                      TABLE 22                                     __________________________________________________________________________                                   evaluation of                                                 purity of cis-Δ9-                                                                 purity of cis-Δ9-                                                                feeling in use                                                octadecenoic acid                                                                       alkenoic acid                                                                          (number of                                                    (%)      (%)     persons)                                         __________________________________________________________________________     Example 106  99.9     100     20                                               Example 107  99       99.5    19                                               Example 108  95       97      18                                               Example 109  90       93      18                                               Example 110  85       90      13                                               Comparative Example 64                                                                      80       86      9                                                Comparative Example 65                                                                      70       78      0                                                Comparative Example 66                                                                      57       66      0                                                __________________________________________________________________________

Examples 111 to 115 and Comparative Examples 67 to 69

Emulsion compositions were prepared by using glycerol trioleates which are oleic acid derivatives having different purities shown in Table 23 as the oily substance and sorbitan sesquioleates and polyoxyethylene (20 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding glycerol trioleates, respectively, as the surfactants according to the formulation described below.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: glycerol trioleate                                                                    50%                                                     surfactants: sorbitan sesquioleate                                                                    8.5%                                                    polyoxylethylene (20 mols) sorbitan                                                                   1.5                                                     monooleate                                                                     watery component                                                               purified water         40%                                                     ______________________________________                                    

                  TABLE 23                                                         ______________________________________                                                      purity of cis-Δ9-                                                                    purity of cis-Δ9-                                            octadecenoic acid                                                                          alkenoic acid                                                      (%)         (%)                                                   ______________________________________                                         Example 111    99.9          100                                               Example 112    99            99.5                                              Example 113    95            97                                                Example 114    90            93                                                Example 115    85            90                                                Comparative Example 67                                                                        80            86                                                Comparative Example 68                                                                        70            78                                                Comparative Example 69                                                                        57            66                                                ______________________________________                                    

Storage stability of the emulsion compositions thus prepared was evaluated. The results on the condition of the emulsion and the storage stability on standing are shown in Table 24.

                                      TABLE 24                                     __________________________________________________________________________             condition                                                                            storage stability on standing, after the specified time                  of emulsion                                                                          30 min.                                                                            1 hour                                                                              5 hours                                                                             24 hours                                                                            72 hours                                      __________________________________________________________________________     Example 111                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 112                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 113                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 114                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 115                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              slightly                                                                       separated                                     Comparative                                                                            good  stable                                                                             stable                                                                              slightly                                                                            separated                                                                           separated                                     Example 67             separated                                               Comparative                                                                            good  stable                                                                             slightly                                                                            separated                                                                           separated                                                                           separated                                     Example 68        separated                                                    Comparative                                                                            good  stable                                                                             slightly                                                                            separated                                                                           separated                                                                           separated                                     Example 69        separated                                                    __________________________________________________________________________

Comparative Examples 70 to 72

Emulsion compositions were prepared by the same method used in Examples 111 to 115 and in Comparative Examples 67 to 69 except that sorbitan sesquioleate and polyoxyethylene (20 mols) sorbitan monooleate as the surfactants were replaced by 8.5% of sorbitan sesquistearate which is a derivative of 99% stearic acid and 1.5% of polyoxyethylene (20 mols) sorbitan monostearate as the surfactants in Comparative Example 70, by 10% of polyoxyethylene (2 mols) nonylphenyl ether as the surfactant in Comparative Example 71 and by 10% of glycerol monolaurate which is a derivative of 99% lauric acid as the surfactant in Comparative Example 72 and the storage stability of emulsion was evaluated. The results are shown in Table 25. The results show that the storage stability of emulsion is inferior when the compounds other than the derivatives of cis-Δ9-octadecenoic acid are used as the surfactant.

                  TABLE 25                                                         ______________________________________                                                condi-                                                                         tion of                                                                              storage stability on standing,                                           emul- after the specified time                                                 sion  30 min.  1 hour   5 hours                                                                               24 hours                                 ______________________________________                                         Comparative                                                                             poor    separated                                                                               separated                                                                             separated                                                                             separated                              Example 70                                                                     Comparative                                                                             poor    slightly slightly                                                                              separated                                                                             separated                              Example 71       separated                                                                               separated                                            Comparative                                                                             poor    slightly separated                                                                             separated                                                                             separated                              Example 72       separated                                                     ______________________________________                                    

Examples 116 to 120 and Comparative Examples 73 to 75

Emulsion compositions were prepared by using ethyl oleates which are oleic acid derivatives having different purities shown in Table 26 as the oily substance and sorbitan sesquioleates and polyoxyethylene (20 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding ethyl oleates, respectively, as the surfactants according to the formulation described below.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: ethyl oleate                                                                          50%                                                     surfactants: sorbitan sesquioleate                                                                    7.5%                                                    polyoxylethylene (20 mols) sorbitan                                                                   2.5%                                                    monooleate                                                                     watery component                                                               purified water         40%                                                     ______________________________________                                    

                  TABLE 26                                                         ______________________________________                                                      purity of cis-Δ9-                                                                    purity of cis-Δ9-                                            octadecenoic acid                                                                          alkenoic acid                                                      (%)         (%)                                                   ______________________________________                                         Example 116    99.9          100                                               Example 117    99            99.5                                              Example 118    95            97                                                Example 119    90            93                                                Example 120    85            90                                                Comparative Example 73                                                                        80            86                                                Comparative Example 74                                                                        70            78                                                Comparative Example 75                                                                        57            66                                                ______________________________________                                    

Storage stability of the emulsion compositions thus prepared was evaluated. The results on the condition of the emulsion and the storage stability on standing are shown in Table 27.

                                      TABLE 27                                     __________________________________________________________________________             condition                                                                            storage stability on standing, after the specified time                  of emulsion                                                                          30 min.                                                                            1 hour                                                                              5 hours                                                                             24 hours                                                                            72 hours                                      __________________________________________________________________________     Example 116                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 117                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 118                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 119                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              slightly                                                                       separated                                     Example 120                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              slightly                                                                       separated                                     Comparative                                                                            good  stable                                                                             stable                                                                              slightly                                                                            separated                                                                           separated                                     Example 73             separated                                               Comparative                                                                            good  stable                                                                             slightly                                                                            separated                                                                           separated                                                                           separated                                     Example 74        separated                                                    Comparative                                                                            good  stable                                                                             slightly                                                                            separated                                                                           separated                                                                           separated                                     Example 75        separated                                                    __________________________________________________________________________

Examples 121 to 125 and Comparative Examples 76 to 78

Emulsion compositions were prepared by using oleyl alcohols which are oleic acid derivatives having different purities shown in Table 28 as the oily substance and sorbitan sesquioleates and polyoxyethylene (20 mols) sorbitan monooleates which are oleic acid derivatives having the same purities as those of the corresponding oleyl alcohols, respectively, as the surfactants according to the formulation described below.

    ______________________________________                                         Formulation                                                                    ______________________________________                                         oily components                                                                oily substance: oleyl alcohol                                                                         50%                                                     surfactants: sorbitan sesquioleate                                                                    8.5%                                                    polyoxylethylene (20 mols) sorbitan                                                                   1.5                                                     monooleate                                                                     watery component                                                               purified water         40%                                                     ______________________________________                                    

                  TABLE 28                                                         ______________________________________                                                      purity of cis-Δ9-                                                                    purity of cis-Δ9-                                            octadecenoic acid                                                                          alkenoic acid                                                      (%)         (%)                                                   ______________________________________                                         Example 121    99.9          100                                               Example 122    99            99.5                                              Example 123    95            97                                                Example 124    90            93                                                Example 125    85            90                                                Comparative Example 76                                                                        80            86                                                Comparative Example 77                                                                        70            78                                                Comparative Example 78                                                                        57            66                                                ______________________________________                                    

Storage stability of the emulsion compositions thus prepared was evaluated. The results on the condition of the emulsion and the storage stability on standing are shown in Table 29.

                                      TABLE 29                                     __________________________________________________________________________             condition                                                                            storage stability on standing, after the specified time                  of emulsion                                                                          30 min.                                                                            1 hour                                                                              5 hours                                                                             24 hours                                                                            72 hours                                      __________________________________________________________________________     Example 121                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 122                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 123                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 124                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Example 125                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              stable                                        Comparative                                                                            good  stable                                                                             stable                                                                              stable                                                                              stable                                                                              separated                                     Example 76                                                                     Comparative                                                                            good  stable                                                                             stable                                                                              stable                                                                              separated                                                                           separated                                     Example 77                                                                     Comparative                                                                            good  stable                                                                             stable                                                                              slightly                                                                            separated                                                                           separated                                     Example 78             separated                                               __________________________________________________________________________

As the results in Tables 24, 25, 27 and 29 show, the emulsion compositions having very excellent storage stability can be prepared by the formulations of Examples 111 to 125, which contain oleic acid or oleic acid derivatives containing cis-Δ-9-octadecenoic acid in high concentrations as the oily substance and oleic acid derivatives containing cis-A9-octadecenoic acid in high concentrations as the surfactant.

INDUSTRIAL APPLICABILITY

As described above, the cosmetic composition of the invention is useful as various kinds of cosmetic materials, such as skin lotion, cream, milk lotion, cleansing foam and the like.

The emulsion composition of the invention can provide an emulsion having excellent storage stability of emulsion. This emulsion can be utilized as a base material for pharmaceuticals, an emulsifying agent for oily materials which are not easily emulsified and the like as well as the cosmetic material. 

We claim:
 1. A composition as a cosmetic which comprises 0.1 to 99 weight % of a first component and 99.9 to 1 weight % of a second component which is water soluble the first component comprising 85 or more weight % of a cisΔ9-octadecenoic acid or derivatives thereof included within 90 weight % or more of a cis-Δ9-alkenoic acid or derivatives thereof, wherein the first component is either insoluble in the second component, dissolved in the second component or emulsified in the second component.
 2. A composition as claimed in claim 1, wherein the first component is insoluble in the second component.
 3. A composition as claimed in claim 1, wherein the derivative of cis-Δ9-octadecenoic acid or the derivative of a cis-Δ9-alkenoic acid is a salt, an amide, an ester or an ether of a cis-Δ9-unsaturated alcohol or a derivative of a cis-Δ9-unsaturated amine.
 4. A composition as claimed in claim 1, wherein the second component comprises water, ethanol, isopropanol, ethylene glycol, propylene glycol, 1,3-butylene glycol, polyethylene glycol, glycercl, sorbitol, a polyglycerol or mixtures thereof.
 5. The composition of claim 1, as a liquid, cream, gel, solid or foam cosmetic composition adapted for application to the skin.
 6. The composition of claim 1, as a skin lotion cosmetic.
 7. The composition of claim 1, as a cleansing cream cosmetic.
 8. The composition of claim 1, as a skin cream cosmetic.
 9. The composition of claim 1, which additionally comprises at least one of a vitamin, an antibiotic, a nutrient, a metallic soap, calcium carbonate, silica, talc, coloring agent and perfume.
 10. The composition of claim 1, wherein the first component further comprises therefor fatty acids other than cis-Δ9-alkenoic acid, or derivatives of fatty acids other than cis-Δ9-alkenoic acids or mixtures thereof.
 11. The composition of claim 1, wherein the first component comprise derivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoic acid which, are salts of the acids, amides of the acids, esters of the acids, cis-66 9-alkenols, ethers of cis-Δ9-alkenols, esters of cis-Δ9-alkenols, cis-Δ9-alkenylamines, salts of cis-Δ9-alkenylamines with an acid or quaternary ammonium salts of cis-Δ9-alkenylamines.
 12. The first component comprises composition of claim 1, wherein the derivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoic acid, selected from the group consisting of: salts of the acids with alkali metals, alkylamines, alkanolamines or basic amino acids; ammonium salts of the acids; morpholine salts of the acids; amides of the acids with alkylamines, alkenylamines, alkanolamines, amino acids or N-methyltaurine; polyoxyethylated or polyoxypropylated compounds of amides of the acids with alkylamines, alkenylamines or alkanolamines; cis-Δ9-alkenoyl peptides; esters of the acids with monohydric alcohols or polyoxyethylated or polyoxypropylated compounds of monohydric alcohols; esters of the acids with polyhydric alcohols or polyoxyethylated or polyoxypropylated compounds of polyhydric alcohols; esters of the acids with sugar compounds; esters and salts of the acids with sterols; esters of the acids with tocopherol, oryzanol, guaiacol, gossypol, terpene alcohols, fluoroalcohols, or isethionic acid; phospholipids wherein the acyl group of a cis-Δ9-alkenoic acid is introduced; cis-Δ9-alkenols and polyoxyethylated or polyoxypropylated compounds thereof; phosphoric esters, sulfuric esters, polyoxyethylated phosphoric esters, polyoxyethylated sulfuric esters, polyoxypropylated phosphoric esters, or polyoxypropylated sulfuric esters of cis-Δ9-alkenols and salts thereof; esters, partial esters or partial ester salts of cis-Δ9-alkenyl alcohols with carboxylic acids or hydroxylated carboxylic acids; ethers of cis-Δ9-alkenols with alcohols, or sugars of other hydroxyl compounds; salts of cis-Δ9-alkenylamines with acids; quaternary ammonium salts having a cis-Δ9-alkenyl group; and, quaternary ammonium betaine having a cis-Δ9-alkenyl group.
 13. The composition of claim 1, wherein the first component comprises derivatives of the cis-Δ9-alkenoic acids, including cis-Δ9-octadecenoic acid, selected from the group consisting of: esters of cis-Δ9-octadecenoic acid with ethanol, isopropanol, cis-Δ9-hexadecanol, cis-Δ9-octadecanol, isooctadecanol, cholesterol and tocopherol; glycerol tri-cis-Δ9-octadecenoate; and, cis-Δ9-octadecenol.
 14. The composition of claim 1 wherein the first component further comprises: fatty acids other than cis-Δ9-alkenoic acid; derivatives of fatty acids other than cis-Δ9-alkenoic acids; paraffin; kerosene; squalene; plant oils; animal oils; lanoline; haze wax; hexadecanol; isooctadecanol; silicone oils; fluorohydrocarbons; polyoxypropylated ethers; cholesterol; tocopherol; dodecandiethanolamide; or polyoxyethylated alkylphenyl ether.
 15. The composition of claim 1, wherein the first component is dissolved in the second component.
 16. The composition of claim 1, wherein the first component is emulsified in the second component.
 17. The composition of claim 15, wherein the first component comprises a cis-Δ9-alkenoic acid or derivative thereof which acts as a surfactant.
 18. The composition of claim 16, wherein the first component comprises a cis-Δ9-alkenoic acid or derivative thereof which acts as a surfactant.
 19. The composition of claim 16, wherein the first component comprises an ester derivative of a cis-Δ9-alkenoic acid which acts as a surfactant.
 20. The composition of claim 1, wherein 85% by weight or more of the fatty acids or derivatives thereof in the composition are cis-Δ9-octadecenoic acid or derivatives thereof. 